N-(heterocyclic alkyl) aminoalkyl silicon compounds and process for their preparation



' 3 008 923 N-(HE'IEROCYCLIC ALKSIL) AMINOALKYL sn.1- CON COMPOUNDS AND PROCESS FOR THEIR PREPARATION Robert J. Lisanke, Buffalo, N.Y., assignor to Union Carbide Corporation, a corporation of New York No Drawing. Filed'June 27, 1958, Ser. No. 744,936 15 Claims. (Cl. 260-46.5)

This invention relates in general to novel organosilicon compounds and to a process for producing them. More particularly, the invention relates to organosilicon compounds containing a N-(heterocyclic substituted alkyl) aminoalkylsilyl grouping wherein the amino group is interconnected to the silicon atom of the silyl grouping through at least three carbon atoms and the amino group is also substituted by a heterocyclic substituted alkyl group, as new compositions of matter and to a process for producing them.

The compositions of the instant invention are organosilicon compounds which contain at least one silicon atom and a N-(het'erocycl-ic substituted alkyl) aminoalkylsilyl grouping as represented by the formula:

, f H V R(CbH2b)CI l(CaH2r)SlE I wherein R is a hydrogen atom'or 1a monoval'ent hydrocarbon radical free of aliphatic unsaturation, a is an integer having a value of at least -3 and preferably from United States Patent 3 to 19, b is an integer of from O to 3 and R is a monovalent heterocyclic group containing no heterocyclic ring of less than 5 atoms and composed of carbon, hydrogen and from 1 to 2 heterocyclic atoms, said heterocyclic group containing no other heterocyclic atoms than nitrogen and oxygen, each silicon atom of the organosilicon compound is bonded to from 1 to '3 oxygen atoms,

each silicon bonded oxygen atom is bonded to either a silicon atom or a carbon atom. of an alkyl group and each remaining unfilled valence of tall silicon atoms is satisfied by no other group than a hydrogen atom or a monovalent hydrocarbon nadical. Such heterocyclic groups include those containing one nitrogen atom in the ring, e.g. pyridyl, indolyl, acridinyl, pyrryl, piperidinyl, quinolinyl and the like; those containing one oxygen atomin the ring, e.g. furyl, benzofuryl, pyranyl, xanthyl and the like; those containing two nitrogen atoms in the ring, e.g. indazyl, pyrimidyl, pyrazyl, cinnolinyl, quinazolyl, phenazinyl, pyrazolyl and the like; those containing two oxygen atoms in the ring, e.g. para-dioxin and the like;' and those containing one oxygen atom.

and one nitrogen atom in the ring, e.g. 1,4-oxazinyl,

'benzoxazinyl, benzisoxazolyL'oxazolyl, iso oxazolyl and the like. Such heterocyclic groups also include those that contain a single heterocyclic ring such as furyl, pyrryl, pyridyl and the like as well as those containing fused rings such as, for example, 1,2-benzopyranyl, indazyl, indolyl, naphthyridinyl, pyr-ido (3-2-b)pyridinyl, carbazyl, acridinyl, quinolinyl and the like.

Compositions of this invention which are monomeric are the organosilanes represented by the formula:

wherein R, R a and b have the above-defined meanings and R represents a monovalent hydrocarbon radical or a hydrogen atom, R represents an ,alkoxy group and n is an integer of from 0 to 2. The organosilanes which are'monofunctional in regard to the silicon atom (i.e. where n=2) are, for example, garmna-N-(indazylmethyl) aminopnopyldiethylethoxysilane, gamma N- 3,008,923 Patented Nov. 14, 196i 2 (benzoturylmethyl) aminopropyldiphenylpropoxysilane and the like. Organosilanes which are difunctional in regard to the silicon atom (i.e. where n=1) are forexample, deIta-N-(pyridyl .methyD-aminobutylmethyldi ethoxysil-ane, gamma-N-(acridinyl methyl)aminopropylphenyldimethoxysilane and the like. The organosilanes which are trifunotion-al in regard to the silicon atom (i.e. where n=0) are, for example, delta-N-(pyridinylmethyl)iaminobutylmiethoxysilane, delta-N-[quinolinyi- (methyl) methyl] aminobutyltributoxysilane, gamma N- (piperidinylmethyl)trimethoxysilane and the like.

The compositions of this invention which are polymeric are the organosiloxanes as represented by the formula:

wherein R, R R, a, b and n have the above-defined meanings. The organosiloxanes of this invention that are trifunctional in regard to the silicon atom (i.e. where n=0) include crosslinked organosiloxanes, for example, delta-N (furylmethyl)aminobutylpolysiloxlane, gamma- N-(indolylmethyl)aminopropylpolysiloxane and the like. Organosiloxanes of this invention which are difunctional in regard to the silicon atom (i.e. where n=1) include the linear and cyclic organosiloxanes. Such linear organosilox-anes are those containing units of the formula:

wherein R, R R a and b have the above-defined meanings. These linear organosiloxanes are, for example, gamma N (pyrrylmethyl)tarninopropylmethylpolysiloxane, delta N benzofurylmethyl)aminobutylphenylpolysiloxane and the like. The organosiloxanes which are difunctional in regard to the silicon atom (i.e. where n=l) also include cyclic organosiloxanes of the formula:

and

wherein R, R R, a, b and n have the above-defined meanings and c is an integer having a value of from 0 to 3, c need not 'have the same value throughout the same molecule and n need not have the same value throughout the same molecule and R can represent the same or different groups within the same molecule. The copolymeric organosiloxane of this invention include end-blocked linear copolymeric organosiloxane oils, copolymeric cyclic organosiloxane and copolymeric, resinous organosiloxanes containing the same or different substituted mono-, diand trifunctional silicon atoms. The compositions of this invention also include copolymeric difunctional silicon guns. Such copolymeric organosiloxane oils are those having the formula:

wherein R, R R a and b have the above-defined meanings, y is an integer, x is an integer of at least 1 and R represents the same or different groups in the same molecule within its meaning as defined above. Such copolymeric organosiloxane oils are, for example: trimethylsiloxy end-blocked dimethylsiloxane-gamma-N- (acridinylmethyl)aminopropylphenylsiloxane oil, triphenylsiloxy end-blocked diphenylsiloxane-delta-N-(furylmethyl)aminobutylmethylsiloxane omega N (indazylmethyl)aminodecylmethylsiloxane oil and the like. Such copolymeric cyclic compositions are, for example, gamma- N (furylethyl) aminopropylheptamethylcyclotetrasiloxane, delta N (indolylmethyl)aminobutylpentaphenylcyclotrisiloxane, gamma-N-[furyl(ethyl)methy-l]aminopropyl .nona-methylcyclopentasilonane and the like. Such co polymeric resinous compositions are, for example:

and the like.

The new compositions of this invention are prepared by the reduction of organo'silicon compounds containing a N-(heterocyolic substituted methylidene)aminoalkyl- .silyl grouping, hereinafter called N-(heterocyclic substituted alkylidene)aminoalkylsilicon compounds by byduogen in the presence of a hydrogenation catalyst according to the following general procedure:

The N-(heterocyclic substituted alkylidene)aminoalkylsilicon compound is charged into a stainless steel autoclave along with a hydrogenation catalyst and the autoclave pressurized with hydrogen gas. The autoclave is then agitated and heated to a temperature sufiiciently elevatedto cause the hydrogen and the N-(heterocyclic substituted a1kylidene)aminoalkylsilicon compound to react thereby, producing the N-(heterocyclic :alkyl)-aminoalkylsilicon compounds of this invention.

In carrying out the hydrogenation according to my invention, any of the well-known hydrogenation catalysts may be employed. I prefer to use such active hydrogenation catalyst as Raney nickel, bis(cyclopentadienyl) nickel, Raney cobalt, platinum-on-charcoal and palladium-on-asbestos. The amount of catalyst employed is not narrowly critical and from about 0.5 percent to about percent by weight of the stai'ting N-(heterocyclic substituted alkylidene aminoalkyl) silicon compounds is preferred. No commensurate advantage is obtained ,using higher or lower amountsof. the catalyst.

tion is carried out is not critical. Temperatures as low as 25 C. and as high as 250 C. are useful; however, temperatures of between 50 C. and 150 C. are preferred. Higher or lower temperatures can be used within the scope of this invention, but no commensurate advantage is gained thereby.

The pressure at which the process of this invention is carried out is not narrowly critical. Pressures as high as 200 atmospheres (3000 p.s.i.) and as low as 1L5. atmospheres (20 p.s.i.) may be used, however, prmsures in the range of from about 20 to atmospheres (300 to 1500 p.s.i.) are preferred. There is no commensurate advantage gained in using pressures above 3000 p.s.i. or below 20 p.s.i.

I prefer to carry out the process of my invention under substantially anhydrous conditions. However, the presence of water is not objectionable, except when thestartin}; materials contain alkoxy groups bonded to the silicon atom thereof. The presence of water is objectionable in the latter instance due to the tendency of the alkoxy groups to hydrolyze when ingadmixture with water;

A solvent is not essential to the process of this invention. However, a solvent may be used to serve as a diluent for the reaction mixture. Such a solvent can be any of the well-known volatile organic solvents which are inert toward the reactants used and which are not effected by the conditions of the process. Such solvents would be, for example: alcohols, Cellosolves (Z-alkoxyethanol) and Carbitols (diethylene glycol monoalkylethers).

The stanting'materials useful in the production of i the compositions of this invention are the ,N-(heterocyclic substituted alkylidene) aminoalkylsilicon compounds which contain units of the formula:

wherein R, R a and b have the above defined meanings and the valences of silicon are satisfied in the manner described above. Thus, for example, these starting materials are monomeric, polymeric and copolymen'c.

The monomeric starting materials useful in preparing the compositions of this invention are the N-(heterocyclic substituted alkylidene)aminoalkylsilanes depict by the formula: p t

where R, R R, a, b and n have the above-defined meanings. These polymeric starting materials include cyclic siloxanes as well as linear siloxanes as, for example where n is l, the starting materials are in the cyclic form having from 3 to 7 such units or they are in linear form having a number of such groupings. Illustrative of the cyclic starting materials are for example tetra[gamma-N- (benzofurylmethylidene) aminopropyl ]tetramethylcyclotetrasiloxane, tetra [delta N (indolylethy1idene)aminobutyl]tetraphenylcyclotetrasiloxane and the like. Illustrative of the linear N-(heterocyclic substituted alkylidene)aminoalkylsiloxane are gamma-N-(pyrrylmethylidene)aminopropylmethylpolysiloxane, delta N-(benzofurylmethylidene)arninobutylphenylpolysiloxane and the like. Where n is 0 in the above formula, the N-(heterocyclic substituted alkylidene) aminoalkylsiloxanes are trifunctional in regard to the silicon atom such as for example, gamma-N-(acridinylethylidene) aminopropylpolysiloxane, delta-N-quinoliny1methylidene)aminobutylpolysiloxane and the like. These polymeric starting materials also include the linear dimeric siloxanes, for example, bisgamma N-(pyrazolylmethylidene) aminopropyldimethyldisiloxane, bis-delta-N-(pyranylmethylidene) aminobutyldiphenyldisiloxane and the like. These polymeric starting materials can be prepared by the hydrolysis and condensation of the corresponding alkoxysilanes.

The copolymeric N(heterocyclic substituted alkylidene)aminoalkylsilic0n compounds that are useful in preparing the compositions of this invention are those copolymeric organosiloxanes containing the units:

is? [S1052 where R, R R a, b, c, and n have the above-defined meanings. R can be the same or different groups within its meaning as defined above and c and n can have different values within their meanings as described above. These copolymeric organosiloxanes can contain various combined siloxane units, such'as, trifunctional N-(hetero cyclic substituted alkylidene)aminoalkylsiloxane units (where n=0) with difunctional hydrocarbon siloxane units (where c=2). These copolymeric oxanosiloxanes .copolymeric organosiloxanes can contain residual siliconbonded alkoxy groups, or they can comprise essentially completely condensed materials.

The N (heterocyclic substituted alkylidene)arninoalkylsilicon compounds useful as starting materials in the production of the compositions of this invention are prepared by the reaction of a heterocyclic substituted aldehyde or ketone with an aminoalkyls-ilicon compound. These N (heterocyclic substituted alkylidene)aminoalkylsilicon compounds are all disclosed and claimed as new compositions of matter in US. application Serial No. 774,901, filed concurrently herewith, as well as a process for producing the same.

The organosilanes in this invention can be reacted with a Grignard reagent to substitute a silicon-bonded alkoxy group by a silicon-bonded hydrooarbyl group according to methods known to those skilled in the art.

The polymeric organosiloxanes of this invention can also be prepared by the hydrolysis and condensation of the organosilanes of this invention.

The copolymeric compositions of this invention can also be prepared by the cohydrolysis and co-condensa-. tion of the monomeric onganosilanes of this invention with hydrocarbylalkoxysilanes. g

The compositions of this invention canbe mixed with the diglycidyl ether of 2,2-bis(para-hydroxyphenyl)propane and the mixture applied to ceramic and cementitious articles and cured thereon to provide wear and stain resistance. The compositions of this invention also find use as anti-oxidants, emulsion stabilizers, ultraviolet absorbing materials and as additives for known silicon products.

The following examples illustrate the invention:

Example I A 300 ml. stainless steel autoclave was charged with gamma N (furfurylidene) aminopropyltrietlhoxysilane (121.7 g., 0.41 mole) bis(cyclopentadienyl) nickel (6.0 g.) and pressured with 1500 psi. hydrogen gas.

sintered glass funnel precoated with 5 g. diatomaceous earth. The filter cake washed with absolute alcohol and the filtrate combined. The ethanol and other volatile materials were removed at atmospheric pressure and the residue boiling above 79 C. was distilled in vacuo through a 10in. insulated Vigreaux column.

Gamma-N- 2-furylmethyl) aminopropyltrietlroxysiiane (B.P. 153-6 c. at 3.5 .n =1.44s3 wa es tained. The structure was verified as gamma-N-(Ziurylmethyl)aminopropyl-triethoxysilane by infra-red analysis and gave the following analysis rfor nitrogen and silicon. Calc. for C H NO Si: N, 4.65; Si, 9.3. Found: N, 4.68; Si, 9.1.

Example ll Example III Gamma N [3-indazyl(methyl)methylidene] aminopropylmethyldiethoxysilane (160 g.) and bis-'(cyclm pentadienyl nickel) (l g.) was changed into a 300 ml.

stainless steel pressure vessel and the vessel pressured to 2000 psi. with hydrogen. The vessel was heated to C. with agitation over a 12 hour period.

After the reaction mixture was filtered and dried '7 gamma N [(3-indazyl) (methyl)methyl]aminopropylmethyldiethoxysilane (N =1.5163, viscosity 7.5 cps. at 25 C.) was obtained.

Example IV Tetra-delta N[(7 methyl-3-indolyl)methylidene] aminobutyltetramethylcyclotetrasiloxane (63 g.) and palladium-omasbestos (3.5 .g.) was charged into a 300 m1. stainless steel pressure vessel and the vessel pressured to 900 psi. with hydrogen. The vessel was heated to 100 C. with agitation over an 8 hour period.

After the reaction mixture was filtered and dried tetradelta N [(7-methyl-3indolyl)methyllaminobutyltetramethylcyclotetrasiloxane CH3 H V 4 (N =1.5021, viscosity 34.8 cps. at 25 C.) was obtained.

- Example V Ninety-five grams of a dirnethylsilico-ne oil containing approximately 1 wt. percent of combined delta -N- [2 benzofuryl(methyl)methylidene]'aminobutylmethylsiloxy units and having the average formula:

was charged into a 300 m1. stainless steel pressure vessel and 4.5 g. of Raney nickel added. The vessel was pressured to 600 p.s.i. with hydrogen and heated to 120 C. for 8 hours with rocking.

The reaction mixture was filtered and dried. A dimethylsil-icone oil containing approximately wt. percent of combined delta N [(2-benzofuryl)(methy1 methyl] aminobutylmethylsiloxy units and having the average formula:

li t i \0 J-N(C4Hs)Si-O (viscosity 35.0 cps. at 25 C.) was obtained.

Example VI One' hundred and one grams of a dimethylsilicone oil containing approximately 10 wt.-percent of combined delta N (9 acridinylmethylidene) aminobutylmethylsiloxy units and having the average formula:

H CH3 was charged into a 300 ml. stainless steel pressure vessel and 10 g. of Raney nickel added. The vessel was pressured to 100 p-.s.i. with hydrogen and heated to 100 C for 4 hours with rocking.

The reaction mixture was filtered and dried. A dimethylsilicone oil containing approximately 10 -wt.-percent of combined delta-N-(9-acridinylmethyl) aminobutylmethylsiloxy units and having the averageiormula:

(viscosity 82 cps. at 25 C.) was obtained.

' Example VII Omega N [3 pyrazolylmethylidene] aminoundecyl triethoxysilane could be reduced with hydrogen using a hydrogenation catalyst according to the procedure given in the previous examples to yield omega-N-[3pyrazolylmethyl]aminoundecyltriethoxysi lane.

Example VIII Gamma N (3 pyranylmethylidene) aminopropyldimethylethoxysilane could be reduced with hydrogen using a hydrogenation catalyst according to the procedure given in the previous examples to yield gamma-N-(3-pyranylmethyl) aminopropyldimethylethoxysilane.

Example IX Delta N (5 oxazolylmethylidene) aminobutylphenyldibutoxysilane could be reduced with hydrogen using a hydrogenation catalyst according to the procedure given in the previous examples to yield delta-N-(S-oxazolylmethyl) aminobutylphenyldibutoxysilane.

Example X Gamma N [3 pyrazolyl(methyl)rnethylidene1aminopropylmethyldiethoxysilane could be reduced with hydrogen using a hydrogenation catalyst according to the procedure given in the previous examples to yield gamma- N [3 pyraZoly-l(methyl)methyl]aminopropylrn-ethyldiethoxysilane.

. Example XI Gamma N [3 benzisoxazolylmethylidene] aminopropylpentamethylcyclotrisiloxane could be reduced with hydrogen using a hydrogenation catalyst according to the procedure given in the previous examples to yield gamma- =N [3 benzisoxazolylmethyl]aminopropylpentamethylcyclotrisiloxane.

Example XII Delta N [2 paradioxinyl(methyl)methylidene] aminobutylnonamethylcyclopentasiloxane could be reduced with hydrogen using a hydrogenation catalyst according to the procedure given in the previous examples to yield delta-N-[2-paradioxiny1(methyl)methyl]aminobutylnonamethylcyclopentasiloxane.

Example XIII wherein R is a monovalent heterocyclic group selected from the class consisting of pyridyl, indolyl, acridinyl, pyrryl, piperidin-yl, quinolinyl, furyl, benzofuryl, pyranyl, xanthyl, indazyl, pyrirnidyl, pyrazyl, cinnolinyl, quinazolyl, phenazinyl, para-dioxin, 1,4-oxazin-yl, benzoxazinyl, benzisoazolyl, oxazolyl, isooxazolyl, 1,2-benzopyranyl, naphthyridinyl, py'rido(3-2-b)-pyridinyl, carbazyl, pyridinyl and pyrazolyl groups, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals containing no aliphatic unsaturation, a is an integer of from 3 to 19, b is an integer of from to 3, said heterocyclic group being interconnected to the group by a carbon tocarbon bond when b is O and when b is from 1 to 3 said heterocyclic group is interconnected to the (C H group through a carbon to carbon bond, each silicon atom of the organosilicon compound being bonded to from 1 to 3 oxygen atoms, said silicon bonded oxygen atoms being bonded to no other atoms than a silicon atom and a carbon atom of an alkyl group and each remaining unfilled valence of all silicon atoms being satisfied by no other groups than hydrogen and monov'alent hydrocarbon radicals. I

' 2. An organosilane of the formula:

wherein R is a monovalent heterocyclic group selected from the class consisting of pyridyl, indolyl, acridinyl, pyrryl, piperidinyl, quinolinyl, furyl, benzofuryl, pyranyl, xanthyl, indazyl, pyriinidyl, pyrazyl, cinnolinyl, quinazolyl, phenazinyl, para-dioxin, 1,4-oxazinyl, benzoxazinyl, benzisoazolyl, oxazolyl, isooxazolyl, 1,2-benzopyranyl, naphthyridinyl, pyrido(3-2-b).pyridinyl, carbazyl, pyridinyl and pyrazoly-l groups, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals containing no aliphatic unsaturation, R is a member of the group consisting of the hydrogen atom and'monovalent hydrocarbon radicals, R is an alkoxy group, a is an integer of from 3 to 19, b is an integer of from 0 to 3, said heterocyclic group being interconnected to the group by a carbon to carbonbond when b is 0 and when b is from 1 to 3 said heterocyclic group is interconnected to the (C H group through -a carbon to carbon bond and n is an integer of from 0 to 2.

3. An organosiloxane containing units of the formula:

wherein R is a monovalent heterocyclic group selected from the class consisting of pyridyl, i-udolyl, acridinyl, pyrryl, piperidin-yl, quinolinyl, furyl, benzofuryl, pyranyl, xanthyl, indazyl, pyn'midyl, py-razyl, cinnolinyl, quinazolyl, phenazinyl, para-dioxin, 1,4-oxazinyl, benzoxazinyl, benzisoazolyl, oxazoly-l, isooxazolyl, 1,2-benzopyranyl, naphthyridinyl, pyrido(3-2-b)-pyridinyl, carbazyl, pyridinyl and pyrazolyl groups, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals containing no aliphatic unsatunation, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals,

a is an integer of from 3 to 19, b is an integer of from 0 to 3, said heterocyclic group being interconnected to the group by a carbon to carbon bond when b is 0 and when b is from 1 to 3 said heterocyclic group is interconnected to the (C H group through a carbon to carbon bond and n is an integer of from 0 to 2.

4. Av cyclic organosiloxane of the formula:

R1 H R1 the group consisting of the hydrogen atom and monovalent hydrocarbon radicalscontaining no aliphatic 1111- I saturation, R is a member of the group consisting of the hydrogen [atom and monovalent hydrocarbon radicals, a is an integer of from 3 to '19, b is an integer of from O to 3, said heterocyclic group being interconnected to the group by a carbon to carbon bond-when b is 0 andwhen b is from 1 to 3 said heterocyclic group is interconnected to the (cbHgb) groupthrough a carbon to carbon bond, and d is an integer of from 3 to 7. 5. A linear organosiloxane containing units of the formula: l

wherein R is a monov'alent heterocyclic group selected from the class consisting of pyridyl, 'indolyl, acridinyl, pyrryl, piperidinyl, quinolinyl, furyl, bernzofiiryl, pyranyl, Xanthyl, indazyl, pyrimidyl, pyrazyL'cinnolinyl, quinazolyl, phenazinyl, para-dioxin, 1,4-oxazinyl, benzoxazinyl, benzisoazolyl, oxazolyl, isooxaztolyl, 1,2-benzopyranyl, naphthyridinyl, pyri-do(3-2-b)-pyridinyl, carb azyl, pyridinyland pyrazolyl groups, R is'a member of 'the group consisting of the hydrogen atom and mono valent hydrocarbon radicals containing no aliphatic unsaturation, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals, a is an integer of from 3 to 19 and b'is an integer'of from O to 3, said heterocyclic group being interconnected tothe group by a carbon to carbon bond when b is 0 and when b is from 1 to 3 said heterocyclic group is interconnected to the (C H group through a carbon to carbon bondt 6. An organosilicon compound containing units of the formulas:

. v B 1111 112,2 [R(OuH2b)-+N(ClHz-J 51-9 2] n 2 and wherein R is a monovalent heterocyclic group selected from the class consisting of pyn'dyl, indolyl, acridinyl, pyrryl, piperidinyl, quinolinyl, furyl, benzofuryl, pyranyl, xanthyl, indazyl, pyrimidyl, pyrazyl, cinnolinyl, quin- .azolyl, phenaz'inyl, para-dioxin, 1,4-oxazinyl, benzoxazinyl, benzisoazolyl, oxazolyl, isooxazolyl, 1,2-benzopyranyl, naphthyridinyl, pyrido(3-2-b) -pyridinyl, carbazyl, pyridinyl and pyrazolyl groups, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals containing no aliphatic unsaturation, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals, a is an integer of from 3 to .19, b isan integer of from 1 1 to 3, said heterocyclic group being interconnected to the group by a carbon to carbon bond when b is 0 and when b is from 1 to 3 said heterocyclic group is interconnected to the (C H group through a carbon to carbon bond, 11 is aninteger of from 0 to 2, c is an integer of from 0 to 3.

7. An organosiloxane of the formula:

wherein R is a monovalent heterocyclic group selected from the class consisting of pyridyl, indolyl, acridinyl, pyrryl, piperidinyl, quinolinyl, furyl, benzofuryl, pyranyl, xanthyl, indazyl, pyrimidyl, pyrazyl, cinnolinyl, quinazolyl, phenazinyl, para-dioxin, 1,4-oxazin'y1, benzoxazinyl, benzisoazolyl, oxazolyl, isooxazolyl, 1,2-benzopyranyl, naphthyridinyl, pyrido(3-2-b)-pyridinyl, carbazyl, pyridinyl and pyrazolyl groups, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals containing no aliphatic unsa'turation, R is a member of the group consisting ofthe hydrogen atom and monovalent hydrocarbon radicals, a is "an integer of from3 to 19, b is an integer of from O to 3, said heterocyclic group being interconnected to the group by a carbon to carbon bond when b is 0 and when b is from 1 to 3 'said heterocyclic group is interconnected to the (C i-1 group through a carbon to carbon bond, x is an integer and y is an integer of at least 1.

8. Gamma N-(2-furylmethyl)aminopropyltriethoxysilane.

9. Gamma N-2-pyridylmethyl) aminopropyltriethoxysilane.

10. Gamma N (3-indazyl (methyl)methyl)aminopropylmethyldiethoxysilane.

11. Tetra delta N [(7 methyl 3 indolyl)methyl]- aminobutyltetramethylcyclotetrasiloxane.

12. A process for producing N(heterocyclic -alkyl)- aminoalkylsilicon compounds containing units of the group by a carbon to carbon bond when b is 0 and when b is from 1 to- 3 said heterocyclic group is interconnected -to the (C i-1 group through a carbon to carbon bond,

each silicon atom of the organosilicon compound being bonded to from 1 to 3 oxygen atoms, said silicon bonded oxygen atoms being bonded to no other atoms than a silicon atom and-acarbon atom of an 'alkyl group and each remaining unfilled valence of all silicon atoms being satisfied by noother groups than hydrogen and monovalent hydrocarbon radicals which comprises reacting a 12 N-(heterocyclic substituted alkylidene) aminoalkylsilicon compound of the formula:

(Cb 2b 'J=N(OsH2s)SiE wherein R, R a and b have the above-defined meanings, and the valences of silicon are satisfied as-above, with hydrogen under-pressure in the presence of a hydrogenation catalyst to produce said N-(heterocyclic alkyl) aminoalkylsilicon compounds.

13. A process for producing N-(heterocyclic alkyl)- arninoalkylsilicon compounds containing units of the formula:

wherein R is a monovalent heterocyclic group selected from the class consisting of pyn'dyl, indolyl, acridinyl, pyrryl, piperidinyl, quinoliny l, furyl, benzofuryl, pyranyl, xanthyl, indazyl, pyrimidyl, pyrazyl, cinnolinyl, quinazolyl, phenazinyl, para-dioxin, 1,4-oxazinyl, benzox-azinyl, benzisoazolyl, oxazolyl, isooxazolyl, 1,2-benzopyranyl, naphthyridinyl, pyrido(3-2-b)-pyridinyl, carbazyl, pyn'dinyl and pyrazolyl groups, R is a member of the group consisting of the hydrogen atom and monovalentthydrocarbon radicals containing no aliphatic unsaturation, a is an integer of from 3 to 19, b is an integer of from 0 to 3, said heteroc yclic group being interconnected to the group by a carbon to carbon bond when b is 0 and when b is from 1 to 3 said heterocyclic group is interconnected to the (C H group through a carbon to carbon bond, each silicon atom of the organosilicon compound being bonded to from 1 to 3 oxygen atoms, said silicon bonded oxygen atoms being bonded to no other atoms than a silicon atom and a carbon atom of an alkyl group and each remaining unfilled valence of allsilicon atoms being satisfied by no other groups than hydrogen and monovalent hydrocarbon radicals which comprises reacting a N-(heterocyclic substituted alkylidene)aminoalkylsilicon compound of the formula:

Rl R (0 b flb) =N-(C A h) S15 wherein R, R a and b have the above-defined meanings, and the valences of silicon are satisfied as above, with hydrogen under pressure in the presence of a hydrogenation catalyst at a temperature from 25 C. to 250 C. to form said N-(heterocyclic =alkyl)aminoalkylsilicon compound.

14. A process for producing N-(heterocyclic alkyl)- aminoalkylsilicon compounds containing units of the formula:

wherein R is a monovalent heterocyclic group selected from-the class consisting of pyridyl, indolyl, acridinyl, pyrryl, pipen'dinyl, quinolinyl, furyl, benzofuryl, pyranyl, xanthyl, indazyl, pyrimidyl, pyrazyl, cinnolinyl, quinazolyl, phenazinyl, para-dioxin, 1,4-oxazinyl, benzoxazinyl, benzisoazolyl, orrazolyl, isooxazolyl, 1,2-benzopyranyl, naphthyridinyl, pyn'do(3-2-b)-pyridinyl, carbazyl, pyn'dinyl and pyrazolyl groups, R is a member of the group consisting of the hydrogen atom and monovalent hydrocarbon radicals containing'no aliphatic uns-aturation, a is an integer of from 3 to 19, b is an integer of from 0 to 3, said heterocyclic group being interconnected to the group by a carbon to carbon bond when b is 0 and when 13 b is from 1 to 3 said heterocyclic group is interconnected to the (C H group through a carbon to carbon bond, each silicon atom of the organosilicon compound being bonded to from 1 to 3 oxygen atoms, said silicon bonded oxygen atoms being bonded to no other atoms than a silicon atom and a carbon atom of an alkyl group and each remaining unfilled valence of all silicon atoms being satisfied by no other groups than hydrogen and mono valent hydrocarbon radicals, which comprises reacting a N-(heterocyclic substituted alkylidene)aminoalkylsili- 1 con compound of the formula:

R1 bH2b)( 3=N-(C.H2-)SiE wherein R, R a and b have the above-defined meanings and the valences of silicon are satisfied as above; with hydrogen under pressure in the presence of a hydrogenat-ion catalyst at a temperature sutficiently elevated to cause said N-(heterocyclic substituted alkylidene)aminoalkylsilioon compound and said hydrogen to react to produce said N-(heterocyclic alkyl)a=minoalkylsilicon compound.

15. A process as claimed in claim 12 wherein the hydrogenation catalyst is selected from the group consisting of Raney nickel, bis-(cyclopentadienyl) nickel, Raney cobalt, platinum and palladium.

Y v No references cited. 

1. AN ORGANOSILICON COMPOUND CONTAINING UNITS OF THE FORMULA: 